The Wanderer
by Deansfavdemon
Summary: The Apocalypse is coming and Dean and Sam are handed impending death and destruction on a plate. With more then half the hunters murdered, they are running out of options. All they have is a name and a prayer, but who said she'd help their side win? D/OC
1. Man Comes Around

The air was getting colder, that's for sure. Dean pulled his leather jacket around him tighter in the October breeze as he and his brother made their way down a street in Havana, Illinois. People were walking past them with wine in their hands and smiles on their faces. The festival across the street was roaring with excitement in the small town, the smell of freshly grilled bratwursts tempting the older Winchester boy more than once.

Orange, red, and yellow leaves crunched beneath their shoes as they held warm cups of cider in frozen hands. The way the air smelt made Dean close his eyes for a moment in pleasure. He loved autumn, no matter how pansy that sounded. Just the smell of burning leaves and the oncoming winter was enough to make even his cold heart smile from time to time.

Nodding his head slightly at a few flirtatious girls, he didn't even take notice to their short skirts or low cut tops. What was wrong with him lately? Usually he would have jumped at the chance, but oh no. Not anymore. Now he was a good citizen who left frozen hooker look-alikes to other guys that walked by.

Sure the upcoming apocalypse might have had something to do with it, or the fact that he had been brutally mauled by hell dogs months before. Seriously though, a few months in hell really killed his libido. Other than a few random flirting moments, he was just doing nothing but hunting.

Sad day when Dean Winchester doesn't want sex.

Downing the rest of his apple cider, he threw the styrofoam cup into a waste basket next to a pretzel stand. Looking up at Sam like a lost puppy, he pouted while looking at the golden brown soft pretzels turning around and around in front of him. His brother quickly smacked the back of his head and pushed him forwards.

"Why the hell can't we eat? I'm starving here Sammy!" He groaned, kicking one foot into the ground while shoving his hands into his pockets.

"We weren't sent here to eat pretzels and cheese Dean. After we're done, I'm sure you can pig out as much as you want to." Sam said somewhat sympathetically, walking against the wind towards a large brick building.

"If I can't, I'm complaining really loudly. Just be warned," Dean mumbled, opening the door to the apartment building as his brother walked in.

Rubbing his hands together to gather some of the warmth from the building, he smiled at a few of the residents. Looking up, he stared at the giant lamp hanging from the top floor that splashed sparkling light against every wall in the place. It shuttered slightly as someone closed a door upstairs.

"It's over here," Sam said suddenly, breaking Dean out of his trance from the lights.

Following his brother over to a wall, they stared at the long call list in the building searching for a certain name. Starting with the first floor, they carefully leafed out all the non-contenders until Sam pointed one of his long fingers at a name towards the bottom of the list.

LEONA PRESCOTT & REBECCA MATTHEWS-- 409

"That wasn't too hard," Dean smiled, walking over to the elevators and pushing an up button.

Rocking back on his heels as it descended from the top floor, he smiled at an old couple as they walked past him. The old lady winked at him behind her husbands back, making Dean laugh in the back of his throat as Sam looked at him weird.

Hearing his phone ring suddenly, he yanked it out of his pocket and looked the caller ID before picking up.

"Hey, Bobby."

"Dean, how are you?" Bobby asked, writing something down as he spoke to Dean. At least that's what it sounded like.

"We're good Bobby, just waiting on the elevator. Do you have any news?" Sam was staring over at him intently, hoping that their mentor had good news, not the opposite.

"Seems another gates been open up in Wyoming son, we're losing them quick," Bobby said sadly, referring to Lillith's ongoing destruction.

"Son of a bitch," Dean swore, quickly saying goodbye and looking for something to punch in the lobby. He seriously didn't need anymore frustration right now.

"Dean, elevator," Sam drawled, pointing to the open doors as he walked forward without him. Giving up on his search for violence, he jumped in along his brother and pushed the button for the fourth floor.

Twirling the silver ring on his right ring finger around, he started wondering how much longer it would be until they lost this battle. Honestly, he knew they weren't doing well right now and hunters were dying left and right. If this meeting didn't work out, they were up shit's creek without a paddle.

"How are we doing this again? We can't mess this up," Dean muttered the last bit under his breath, running both hands through his hair as he wished the elevator to go faster.

"He said he'd meet us up here, right?" Dean nodded up at his brother, "So we just make small talk I guess. Maybe we tell her we're waiting for her roommate to get back. It did say Leona and Rebecca."

As Sam shrugged his wide shoulders, Dean tried to come up with a good story to make the girl trust them long enough to get their point across. Maybe act like Rebecca's boyfriend? Brother? Something had to work.

"Right, gotcha," Dean smirked, checking down the hallway when they reached the fourth floor. It looked clear, from what he could tell at least. No demons, that had to be good.

They walked down a few hallways before they came to a bright blue door with bronze numbers that read 409. Looking up at his little brother, he shrugged his shoulders and watched as Sam knocked on the door rapidly with his knuckles.

"She's not going to attack us you know. Well, at least not that we know of." Sam's forehead creased a little, listening for footsteps nervously.

"I reckon we should have brought flowers. You know, in case she's one of those girly girls," Dean joked, standing up straighter when the door opened. A short brunette girl looked up at them carefully, her glasses on the end of her nose as she smirked.

"I was wondering when you two would show up."


	2. I've Been Everywhere

**Disclaimer: All goes to Kripke and the amazing Supernatural writers except the plot and my own characters.**

_Author's Note: This story is taking place this season right after Episode Two. If you're not caught up, please beware of spoilers and so on. I hope y'all keep enjoying this, and keep your reviews coming!!_

* * *

Taken back as she continued smirking, Dean looked to Sam and then back again at the small girl now gesturing to come inside. Walking in after his brother, he eyeballed the place to make sure nothing weird was up. All they were told was that they were meeting a girl…not a psychic.

Along the main wall hung posters, bookshelves, and a flat screen TV. A large lime green couch placed itself in the center of the loft with a white shag rug that Dean imagined was very comfortable to lay on. Turning back to the kitchen, he couldn't seem to find anything that shouted that she was out of place.

"Are you totally wigged that I knew your names?" Leona smiled, settling down in a zebra print chair that made Dean cringe inside. She didn't have much style, he knew that.

"Totally," Dean mocked back, looking down at her t-shirt to see Led Zeppelin staring back at him.

"Yeah, thought so. You can skip the story about how you're here to see Rebecca or whatever you lamely came up with. Just tell me why you're here, and I'll cooperate to the best of my abilities," she grinned again, standing up as a teapot rang in the kitchen.

Dean followed the sway of her hips snug in their skinny jeans as she padded barefoot across the hardwood. Just because he didn't flirt, it didn't mean he didn't appreciate a well fitted pair of denim. Her long brown hair was tied up on top of her head in a purple ribbon, lazily bobbing around as she poured her drink. He felt slightly hypnotized by the way it moved.

"We actually are waiting for someone to get here first," Sam spoke up, settling on the Kermit the Frog couch. Dean reached back to his belt to just make sure his gun was there, calming him down when the cold metal bit into his hand.

"If I knew I was throwing a party, I would have made quiche," Leona joked, walking over with a mug tight in her hands and settled back in her chair. Her dark blue eyes stared up at him kindly as he shook off her staring and turned towards the wall.

"So, you like rock?" Dean asked lamely, staring at a AC/DC poster that hung next to a Blue Oyster Cult.

"Certain bands, yeah. If they're good live, I'm a fan," she said seriously, pushing her thick brown frames back up her nose. He took a closer look at the wall and saw a picture of another girl rocking out at a concert.

When he was about to ask if it was Rebecca, he felt the room change. It wasn't like it got colder or that he felt the presence of something evil. On the contrary, by now he knew that feeling only brought good. Or so what God called good. He still wasn't so sure.

Turning towards the front door, it slowly opened again to show a tall man standing very calmly outside it. His business attire put him out of place as well as the way he walked into the room. The air of pride and dignity that radiated off of him made Dean feel like heaving. Not to mention that the man rarely brought good new.

"Leo, good to see you're still in well form," Castiel spoke directly to the girl, ignoring Dean and Sam altogether. This is when Dean realized that the angel hadn't been telling him everything. He got that clearly from the look on Leona's face, and the fact that he should have already figured it out.

"Can't say the same, Cas. You look, what's the word? Older than the last time I set eyes on you. Ancient in fact, absolutely dreadful. A demon beat up on you recently?" Leona said, batting her eyelashes in a patronizing sort of way. Something Dean would never do to someone he knew burned peoples eyes out. Or anyone.

He did not bat eyelashes.

"You know what's been happening on earth, do not pretend you don't. You should already be preparing, and yet you sit here conversing with humans as if you've become one."

Castiel seemed as if he'd been betrayed by Leona, puffing out his chest as if wounded by her words. Dean shook his head as if to clear his mind, looking back over at Sam and Leona with a look of confusion on his face. Sam looked blank, staring back and forth from the tall angel to the girl.

"What the hell is going on here?" Dean shouted, gesturing at anyone who would take notice. Being stuck in the dark was one of his most hated things. You either tell him what's going on, or he leaves.

"Tsk tsk Dean. What would God think of his pride and joy if he went swearing about?" Leona asked, standing back up to put her empty mug in the sink.

"One, girly, I'm no one's pride and joy. Two, who are you? We were sent up here saying you could help, not that you were some crazy girl with a fetish of pissing off angels," he growled slightly, fed up with the game of cat and mouse Leona and Castiel were playing.

"Oh, Cas, you didn't tell them who I was? You just assumed they could woo me with their looks to help you out? Is that it?" Leona asked seriously, playing with a chain that hung loosely around her neck. Her eyes were wide on her small face, blinking slowly as she awaited an answer.

"Lust has always been something you've never been able to deal with."

As he said this, Leona's face turned a bright shade of red and if looks could kill, Dean had no doubt that would be the end of the angel. She stalked forward suddenly, grabbing a hold of his arm and pulling her with him up to Castiel as he heard Sam jump up from his seat, ready for a fight.

"You sent them to tempt me, Angel? To make me fall into lust so strongly that I'd bend at their every will? Are you serious Castiel? I'm not as ignorant as you think. This boy," she shook his arm harshly, making him wince in pain, "has committed more sins than anyone in this building. Maybe even this town. Are you really trying to make matters worse? Are you trying to send me to hell?"

Dean looked quickly back at Sam, questioning him with a raise of the eyebrows. Sam just shrugged back at him, confused as he was. God what he wouldn't do for an explanation and a cold beer right now. Maybe even something good on TV…he just wanted a day off.

"Only He can send you to Hell Leo, not I. Though, I will not lie and say I wasn't trying to tempt you. We all know how well you were perceived before you ended up here. Most of us are happy you're gone, there's no getting around that." Castiel spoke again, grazing a finger under her chin like a small child.

"Well, I'm not doing any of your dirty work Cas. Not for you, and not for the Winchester's. I get to pick my own side on this now, thanks to you. So if I choose Lucifer, that's all up to me," Leona spat, still holding onto his arm like it was the only thing keeping her up. He, for some reason, felt bad for her.

"You would not choose him above God, we all know that. Just help these boys, and you shall be given back your wings."

"I still have my wings," she said coldly, confusing Dean a little further.

"You're an angel?" Sam said from behind them, making Dean part of the game again. Now he knew where this was going.

"Technically, yes. But I don't live upstairs anymore, if you catch my drift," she said solemnly, loosening her grip on Dean's arm but still not letting go.

"She has fallen Sam, she disgraced God and was sent here as punishment," Castiel continued, making Leona slump even more.

"Being on earth is punishment?" Dean asked incredulously, looking around her house to gesture that her life wasn't all that bad. Seriously, if she had been homeless and hadn't eaten in a year…now that would be punishment.

"Losing my powers and becoming human…that's my punishment."

She finally let go of his arm completely, walking away from all of them towards the back of the house before closing a door. Looking back from her hallway, Dean looked over at Castiel to suggest he had a lot of explaining to do. Which in fact, he did.

"I'm sorry I didn't tell you what Leo was, but I didn't think you'd come here if I did," he said with an emotionless face, settling into the zebra chair awkwardly.

"So just sending us blindly to some demon angel was your best idea? Not really using your brain are you?" Dean said exasperatedly, throwing his arms up in the air as he began to pace.

"She is no demon, Dean. In fact, Leo is an angel that thwarted demons when she was still in full power. The fact is, we're willing to give back her power if she fights with us. If there's even a suspicion she'll choose the dark before the light, we'll be out of luck."

Dean looked over to Sam again, his little brother on the verge of a question. Dean walked over to the window while Castiel told Sam the plan on convincing her to fight with them. Staring down at the people at the Wine Festival, he started to think about if they lost this fight.

How long would he live? Would he be sent straight back to hell? What about Sammy? Or Bobby? The whole thing was making his head ache as he closed his eyes and set it against the cold glass. It cooled his hot face, but he still ached all over.

"I hate you, you know," he heard her voice say, standing next to him suddenly as if appearing out of thin air.

"You hate me?" Dean asked tiredly, not turning his face to look at her. He needed a bed and about three weeks of sleep right now. Not some confessing fallen angel.

"Yeah, I do. I've watched your family for years you know, out fighting demons in the real world. I always wanted to do that, but nope. I sat up in a freaking cloud basically smooshing them with my fingers. In a matter of speaking," she laughed a little, his eyes looking at her hands as the made a pinching motion. He could only imagine.

"So you hate me for being able to kill demons with my bare hands?" He smirked, feeling the spark of pre-hell Dean come back.

"No."

"My devilishly good looks?"

"Please."

"Then what?" She had his full attention now, her rose lips curled into a smile as she winked at him.

"That's a secret you're not going to be getting out of me anytime soon, Winchester."

And that's when he knew.


End file.
